Jessie's Wonderful Life
by WolfDraco37
Summary: Jessie's life was simply perfect, she had everything she ever wanted… and it was all thanks to her boy toy, Ash Ketchum. Hardcore/Explicit Lemon. Strong Language. One-Shot.


**This is mostly just a Lemon/Smut story involving Ash and Jessie, not much plot or story, so if you don't like that then don't read this.**

 **Anyways, I haven't seen many Jessie/Ash fics so I was like f%#$ it I'll do one, and this is what I came up with, so yea…**

 **Things to know:**

 **\- This is entirely an A/U story.**

 **\- Jessie worked alone in TR (so James and Meowth don't exist in this story).**

 **\- The same goes for Ash; he traveled alone and never traveled with Brock or Misty, etc...**

 **\- Ash grew up as he traveled, so he is 19 yrs old in this fic – Jessie is 26.**

 **\- Ash is OP, I don't know how to explain it so just read the story to find out why I'm saying he's OP.**

 **\- Finally, towards the end you'll find out how they ended up being together.**

 **Ok that's it, hope you enjoy.**

* * *

 _ **HOENN REGION**_

 _Jessie's Mansion - Bathroom_

Jessie was sitting down on her golden bathtub, with her slim sexy legs dangling off on the side, relaxing and greatly enjoying the way the warm refreshing water felt against her light tanned naked body. She opened her eyes, having had them closed as she relaxed, and looked at the digital clock that was on top of the door leading to the bathroom, she smiled when she saw the time.

" _He should be arriving soon… good, I've been craving a good fucking."_ Jessie thought to herself before she submerged her head underwater.

She stayed submerged for a few seconds before she quickly resurfaced and stood up from the golden tub letting all the water flow down her smoking hot, athletic body. After most of the water dripped off her, Jessie got out of the bathtub and walked over to her giant three-panel mirror where she began drying herself off. After quickly drying off her naked body, Jessie moved on to her signature crimson red hair, after she was finished with that she looked at her own reflection and couldn't help but smile.

"Well Jessie, you are one sexy bitch." She said out loud as she started checking herself out.

First, she admired her flawless hourglass figure before moving to her flat slim stomach, next she pressed her huge double-D tits together making them seem even bigger than what they already were, and finally she turned around and looked at her big, nicely round ass. Jessie admired it for a few good seconds, even jumping up and down a few times making it clap, before she placed her hand on her left butt cheek and gave it a nice hard slap causing it to jiggle for a quick two-seconds. She turned back around, raised her hands to her hair, and began pretending she was in a photoshoot by doing a bunch of different erotic poses.

"Alright…I better get ready." She said after a while, doing one final sexy pose.

After that she got ready, by putting on some sexy black stockings and nothing else, and went to her room to wait for her boy toy to arrive.

"Hopefully the _twerp_ doesn't take too long. I'm so horny already."

 **J.W.L**

 _Unknown Air Route_

A young man, in his late teens, was mounted on the back of a white and blue legendary Pokémon: Lugia, and was flying rapidly towards a giant, secluded, white mansion that was located on a mountain top. He was wearing a black shirt, a navy blue sleeveless hoodie over it, dark gray pants, blue sneakers, and had on a black and red hat backwards. As the young man kept getting closer to his destination he couldn't help getting aroused and excited, he just couldn't wait be with _her_ again, after 5 days of being away, and also because he wanted to show _her_ that he had completed the mission of capturing the three rare and legendary Pokémon that she had sent him out to get, which were in his Pokémon belt right now. He was hoping, although he was certain, that she would reward him by pleasuring him or allowing him to pleasure her, just like she always did whenever he completed an assignment.

"God, I just can't wait to have your hot sexy body again my _crimson_ haired queen." The teen said to himself in a daydreaming type-of-tone.

So, with that in mind, he commanded Lugia to fly faster towards the mansion.

 **J.W.L**

 _10 Minutes Later…_

 _Jessie's Mansion – Master Bedroom_

" _Oh god, he's soooo fucking good at thissss!"_

Jessie was feeling so much euphoric bliss that she had to bite her bottom lip just to try and muffle a moan that was threatening to come out, she was currently laying down on her stomach completely naked with her black stocking covered legs spread open on top of her plush king size bed, so she closed her eyes and decided to think about something that would take her mind off the wonderful sensation she was feeling. She began thinking about how great her life had turned out after she had seduced _him_ and made him her lover (more of a boy toy) and manservant; thanks to her conquest, she was able to quit Team Rocket and obtain everything a young, sexy, hot woman like her could possibly want. She was filthy rich, had many gems and diamonds, owned all kinds of legendary Pokémon, and best of all her lover fucked her extremely well whenever she wanted. Her lover was also the one responsible for giving her and maintaining her luxurious lifestyle, he gave her and did anything she asked for, and all Jessie had to do was have sex with him, which of course she was more than happy to do. What Jessie absolutely loved most about her lover was that he was not only very eager to please her but was also very adventurous and would do many things that her previous sex partners wouldn't. The proof of that was happening right now; Jessie had her lover laying down, also naked, in between her legs with his face buried in between her big round ass cheeks licking her asshole like some crazed possessed Pokémon.

" _Ohhhhh Yesss!_ You sure do like licking my ass, don't you…Ash." Jessie moaned sexily as she turned her head sideways to face her lover, her lover, which was a raven-haired young man, lifted his face from her ass cheeks revealing a satisfied expression on his face. He had light brown colored eyes, two zig-zag lines on his face one on each cheek, and he had the signs of a goatee beard appearing on his chin which, right now, was dripping with her pussy and asshole juices.

"Fuck yeah I do. It's so… umm it's so freaking wonderful." Ash responded enthusiastically before he once again grabbed and pulled her ass cheeks apart showing him her tight little butthole, licking his lips Ash buried his face in her ass again. This time, instead of tongue fucking her asshole right away, he first traced the outline of it with his tongue, this caused Jessie to scream and laugh with pleasure. While she enjoyed his oral work Ash would simply moan and moan "Hmmm" as he found the taste of her ass to be absolutely amazing. He only traced it for a few seconds before he couldn't take it any more and he stuck his entire tongue as deep as he possibly could inside her.

When Jessie felt his warm wet tongue enter her she moaned sexily causing her mouth to form a perfect O shape, her ass and legs also began shaking with pleasure and were only calmed down when Ash grabbed her inner thighs. Soon after Ash started lashing his tongue wildly inside her causing her to wiggle her butt side to side from the intense feeling, and it wasn't long before it was too much for her to handle and she proclaimed that she was about to cum.

"Oh Ash I'm so close…I'm so fucking cl- oh god I'm gunna cum! I'M GUNNA CUM!" Jessie screamed as she grabbed a handful of his black hair and shoved his face even deeper into her butt . Ash didn't mind at all, he was going to do that either way, so he just used this opportunity to stick his tongue even further inside her, and a few seconds later she started cumming.

Jessie moaned loudly with ecstasy when her body started convulsing as she started cumming and squirting out her juices all over the mattress and on Ash's mouth, since Ash was licking her asshole most of her cum splashed against his lower jaw and chin, which he was more than happy to slurp up. After tasting and swallowing all of her delicious juices Ash, wanting to prolong her high for as long as possible, began licking her pussy gently. Jessie rewarded him by tightening her ass cheeks around his face and by telling him how good his tongue felt.

As he kept licking her, Jessie laid her head down sideways, with a satisfied smile on her face, and closed her eyes as she enjoyed the wonderful feeling her pussy was receiving from his tongue.

"Now, tell me…where you able to catch Groudon, Kyorgre, and Rayquaza?"

"Yeah _(lick)_ I _(lick)_ was." Ash responded excitedly after every lick that he gave her pussy.

"Nice job, I knew you wouldn't fail me."

"I would never _(lick)_ fail you _(lick)_ you're body _(lick)_ is too precious _(lick)_ for me to fail _(suck*)_ " he answered just before he pressed his lips against her and sucked on her pussy lips, causing her to giggle and moan sexily.

"Hmmm…Good. That's what I like to hear."

 **J.W.L**

Ash was in absolute heaven right now, being able to lick, tongue fuck, and taste Jessie's asshole was one, if not, his greatest dirtiest pleasures, nothing even came close to making him feel as happy or as good as he was right now.

He was currently licking her delicious pussy, after having made her cum by licking her asshole a few seconds ago, and as he licked her he was thinking about how unbelievably lucky he had been today. As soon as he had arrived and entered Jessie's mansion he had heard her loud moaning echoing throughout the house, so by following her cries of pleasure he ended up in her bedroom. Which when he went in, he found her laying down on her stomach with nothing but some sexy black stockings on playing with her pussy. As soon as Jessie had seen him she had ordered him to strip naked and to come on the bed with her so that he could begin licking her ass. Ash was left shock by her command, it had nothing to do with her ordering him to lick her asshole because even the Pokémon gods knew how much he loved her ass, it was actually because it was very rare for Jessie to allow him to pleasure her without him even showing her the _goods_ that he had been sent out to get. But, quickly getting over the shock, he took off all his clothes, jumped on the bed with her, and began wildly licking and motorboating her butt cheeks.

That was how he had ended up where he was now, which was licking and cleaning up her pussy after having made her cum, however, as he continued licking his cock began throbbing painfully reminding him that he was still aroused and that he wanted to cum too. So giving her pussy one long, final lick he stopped what he was doing, got on his knees, and pleaded her to let him fuck her ass.

 **J.W.L**

After a few minutes of feeling his tongue do all kinds of twirls inside her pussy Jessie felt Ash stop and get on his knees behind her. Then she heard his request.

"Please Jessie let me fuck your tight asshole." Ash asked with a hint of desperation in his voice.

Jessie smiled, she loved knowing that no matter how horny or aroused he was, Ash would always ask her for permission before he did anything, it made her feel, even though she was, in complete control over him.

"Well…you did lick it really good, and you made me feel even better by licking my pussy after I came, and you also captured all three of the legendary Pokémon. So I guess you deserve it…" she said as she reached, using both hands, for her ass cheeks and spread them apart showing him her dripping wet pussy as well as her little puckered asshole "…knock yourself out." she finished with a seductive voice while turning to look at him.

Ash licked his lips as he saw both of her womanly charms "Your pussy and ass look so damn hot." he said before he crawled on top of her, grabbed his cock, and guided his bulbous head to her asshole. He carefully pushed it in her causing Jessie to moan softly, and she wasn't alone, Ash had to grit his teeth to prevent himself from moaning. Just from barely being inside of her he was already able to feel how tight she was. So, after 5 seconds to gather himself, he gripped the sheets that were on either side of her head and then very slowly began to slide his entire cock into her.

"OH SHIT…THAT FEELS SO GOOD!" Jessie moaned with pleasure as she felt inch after inch of his cock go inside her, Ash simply grunted and growled from the wonderfully tight feeling he was receiving from being inside her ass _. "Damn her ass is…aughh… so fucking amazing."_ Ash thought as he slowly began thrusting into her, it didn't matter how many times he had fucked her in the ass, Ash never got tired of it, it was so hot and extremely tight, it was simply _magnificent_. While he got used to her tight ass, he thrusted into her at a slow pace but after getting used to it he steadily began picking up speed, and it wasn't too long before Jessie was made to scream like a dirty slut as he began pumping into her at full speed. As he thrusted into her he leaned down a little and began planting little kisses to the back of her neck as well as her shoulders causing her moan very hotly.

After kissing her shoulders for a while he brought his lips close to her ear "Your asshole… _fuck_ … is so tight!" he whispered huskily just before he thrusted into her deeply, somehow, that caused Jessie to lose it because the next thing he knew she was backing up, shaking, and rubbing her ass against him. " _AHHH_ YES DO THAT AGAIN ASH! THAT FEELS SO GOOD! SHOVE ALL 8' INCHES OF YOUR DICK INSIDE ME!" Jessie began screaming loudly, feeling her ass rub against him, Ash couldn't help but growl from the pleasure that it caused him. However, quickly recovering, Ash did as she asked and began using all his force to ram his cock as deeply as he could inside her ass. It went in so deep that it not only caused Jessie's eyes to role to the back of her head, but it also caused her to feel blissful pain. He kept pumping into her non-stop for the next few minutes, Jessie screamed and moaned like a whore the entire time, until finally he felt his balls start churning letting him know that he was going to cum real soon.

"Jess- Jessie I'm gun- I'm gunna cum!" Ash barely growled out, Jessie looked back at him and said "Me too, do it in my ass Ash! CUM INSIDE MY ASS!", Ash locked eyes with her and nodded before he started going faster and faster as he felt his climax rapidly approaching. After thrusting into her a few more times he felt his cum start traveling from his balls all the way to the tip of his dick, so just before he came he pulled out most of his dick, only leaving the tip in, and then using his last bit of strength he rammed his entire cock into her asshole. As soon as he entered her he gritted his teeth and moaned as he started shooting spurt after spurt of cum inside her, Jessie, for her part, screamed with pure ecstasy as she also started cumming when she felt his hot cum start painting her butthole. Ash stayed inside her until he finished cumming, which took about 2 minutes, and even after he was done he didn't pull out, he just laid down on her back and began kissing her shoulders softly as he relaxed.

When Jessie felt Ash lay on her back she also laid her head down and began resting a little bit, after a few minutes of catching her breath she felt her clit start tingling and her pussy heat up _"Damn it, even after having my ass fucked I'm still horny…oh well I guess Ash will just have to fuck my pussy next."_ Jessie thought as she smiled. Feeling him kiss her shoulders Jessie raised her head off the bed and turned sideways to face him "You better not be tired yet, because I'm still horny and I want you…" she started as she tighten her butthole around his cock making him get hard again as well as make him hiss with pain and pleasure "… to fuck my _wet, hot_ , _tight_ pussy." she finished with a very, very seductive and tempting voice.

"When it comes to fucking your hot body, I'm never tired." Ash replied as he pushed himself up and then pulled himself out from her ass, which, when he did that he saw a nice glob of his white cum come out and drip down to her pussy and eventually fall to the mattress. "That's hot." he said without thinking, Jessie just smiled before she flipped her body over, now she was laying down on her back, exposing to Ash her giant glorious tits "Are these hot too?" she asked playfully while pressing them together. "Very" Ash replied, Jessie just laughed as she slowly slid her right hand down her flat stomach until she reached her pussy lips, then using her middle and pointing finger, she spread them open showing him her pink insides. Ash was left salivating like a thirsty lickitung as he saw her beautiful pussy.

"Now, how about you use that big dick of yours to pound this little pussy, hm?" Jessie asked in an alluring tone, Ash didn't even look at her or answer her he just nodded his head as he kept staring at her pussy. After a few seconds Ash finally got it together and grabbed his, now hardened, cock and guided it to her dripping entrance. Just like with her asshole, he inserted only the tip first so he could give himself some time to relish how wet, hot, and tight her pussy was. However, unlike before, after getting somewhat used to the wonderful sensation instead of sliding into her slowly he leaned down, so now his face was mere inches from hers, and then he thrusted his dick as hard as he could inside of her.

"OHHH FUUUCK YESSS!" Jessie screamed with pleasure when she felt his entire cock penetrate her, so much so that her back arched a little, _"Oh fuck"_ Ash thought as he gritted his teeth, he knew her asshole was tighter but her pussy could certainly make a case for itself. What made it worse (or better) was the fact that her pussy was also very wet yet still very, very hot; words couldn't even begin to describe just how divine Jessie's pussy felt.

After a few seconds of not moving, Ash finally began pumping his cock in and out of her, this time he didn't go too slow or too fast he went at a pretty decent pace, causing her to moan and groan after every thrust. It was only after 5 minutes of thrusting into her that Ash couldn't take it anymore, he wanted to pound and conquer her pussy, so he pulled his cock halfway out of her pussy and then quickly rammed it back inside her. His cock went so deep that it kissed her cervix causing her slight pain but even greater pleasure. He kept doing that over and over again that the only thing that was heard throughout the room was Jessie's screaming and a repeated slapping sound that was made from his balls constantly smacking against her ass.

"RIGHT THERE ASH! OHH YESSS RIGHT THERE! DON'T STOP!" Jessie screamed and moaned like a dirty whore as she wrapped her luscious legs around his waist, hearing her praises drove Ash wild with lust so he thrusted faster, if that was even possible. As he kept pumping into her he couldn't help it when he started getting hypnotized by her giant tits and little pink nipples moving up and down after every thrust that he gave her. So, it wasn't a big surprise when he leaned his head down and captured her right nipple in his mouth and began sucking on it, all while never once stopping from fucking her.

The screams that Jessie unleashed, when he started sucking her tit, where like music to Ash's ears, it was the sexiest sound he had ever heard, and it was even better knowing that it was because of him that she screamed like that. After sucking on her right nipple for a while he switched to her left one and did the same thing. It was only then that Jessie began blabbering stuff to make him lose it.

"You love my… _oh yes that's the spot_ …tight pussy don't you Ash." She asked him using a very lewd voice, "Of course I do, I'll do anything to have this pussy." he quickly replied. Smiling, Jessie couldn't resist asking "Do you regret me… _augh_ …seducing you and making you… _ahh_ … my manservant and boy toy?", Ash opened his eyes, having had them closed as he sucked on her nipple, and had a quick memory recollection of the day she seduced him and made him hers.

He could remember it like it was yesterday.

[ **Memory** **Recall – 4 years ago** ]

He had just finished capturing a powerful Salamence, with his sceptile, and was celebrating like a little kid, even though he was 15, when out of nowhere he was knocked out by sleeping gas. When he woke up he discovered that he was in some type of cabin or cottage, completely naked, and tied to a bed from all his limbs. It was when he tried to escape that his capturer, Jessie, made herself known and when he saw her he got really embarrassed because she was also naked, but for someone reason he just couldn't look away. Once he slightly got over his embarrassment he demanded to know why he was here and what she was going to do to him to which she replied coyly "I got plans for you twerp". After that she got on the bed with him and commenced to pleasure him sexually, she licked and sucked his cock, placed his cock in between her breast and gave him a titjob, and she even did a few kinky stuff like rub his dick with her feet, basically giving him a footjob. Of course in the beginning he had protested, because she was practically raping him, but being a healthy growing teen his hormonal body started enjoying the pleasure he was receiving and it wasn't long before he stopped trying to resist her. It was only then when she stopped pleasuring him and told him that if he promised to work for her she would make him feel even greater pleasure than what he was already feeling, being too far gone, he agreed without hesitation. And it was that same day that he had sex for the first time with a woman; it was also the day that he became addicted to sex, which she used as an advantage to make him submit even more. After that day he did everything she commanded him to do, it didn't matter what it was, the first thing that she ordered him was to give her his precious Pikachu, which he quickly did, then she made him give up his dream of becoming a Pokémon master, which he also did. She used his sex addiction to make him do all her bidding, if she wanted him to steal something he did it; if she wanted him to capture a certain Pokémon he did it. That's exactly how she became filthy rich, she would have him capture powerful rare Pokémon for her and then she would sell those Pokémon (Ash's Pikachu being one of them) for great amounts of money, usually in the Pokémon black market. It was only when he became a strong and powerful trainer that she started sending him out to capture legendary Pokémon. She, of course, would keep the legendaries because she wanted to be the most powerful and feared person in the entire world.

That was pretty much how his new life as Jessie's boy toy and manservant would go; if he fulfilled her wishes she would reward him with her body, and with the reward being sex he always fulfilled her wishes.

[ **Memory Recall End** ]

Releasing her nipple from his mouth and stopping his thrusting he raised his head and answered her "Are you kidding? How could I regret being seduced by you, thanks to you I know what true pleasure is… if it wasn't for you I would probably still be out traveling through a whole bunch of regions meeting girls and not even fucking them because I would be too focused on Pokémon training or something." He said while looking straight at her. Jessie smiled wickedly "What about Pikachu, don't you miss him?" she asked, "I don't give a fuck about him or any of my Pokémon anymore, I only care about serving you and pleasuring you." Ash responded. "God I love it when you sound so…so evil, it makes me feel so hot…speaking of which, how about you get back to fucking my pussy." Jessie said as she squeezed her pussy walls around his dick making him moan. "With pleasure." He said just before he started thrusting into her once again, he started off slow but very quickly picked up the speed until he was plowing into her again.

This time, as he rammed into her, he leaned his face down again and began kissing and licking her delicate neck causing her to moan softly. After hearing Ash's responses to her questions, Jessie was greatly enjoying even more as he fucked and kissed her, she loved knowing that, there was no doubt now, she literally had Ash eating out of the palm of her hands.

They continued fucking each other for the next 10 minutes before both of them felt their climax approaching, Jessie tighten her legs around his waist and yelled that she was about to cum "I'm gunna cum! I'M GUNNA CUM!", Ash gritted his teeth "Sh-shit me too." He growled out. After a few more thrust Jessie wrapped her arms around his neck and screamed "I'M CUMMMINGGGG!", Ash only hissed in reply as he felt Jessie's pussy become even tighter around his cock, and then he felt her juices gush out and splash against him. As soon as he felt her juices wash over his dick he lost it and growled loudly as he buried himself as deep as he could inside her pussy and began releasing his cum, he unloaded so much that he felt as it overflowed her pussy and then start leaking out of her.

Both of them stayed connected until their high's passed and right when he was going to pull out Jessie grabbed his head and pulled him down into a hot passionate kiss. Ash was surprised but recovered fast and kissed her back with just as much intensity. They stuck their tongues in each others mouths and began fighting for dominance, which of course she won. After a few seconds they broke the kiss, only a string of saliva connecting their lips, and it was then when he finally pulled his dick out of her. As he pulled it out he saw their mixed love juices come out of her and drip down to the mattress below, if he hadn't came twice already he might have gotten aroused again but he was tired so he just laid down on his back right next to her and began to catch his breath.

He had just been laying down for a few seconds when he heard a lighter turn on and then he saw a puff of grey smoke. When he turned his head he saw that Jessie had lit up one of her fancy black cigars (the ones that look like wands) and had begun to smoke it.

"Why do you always smoke after we have sex?" Ash asked her.

"Because it makes this…" she reached for her pussy with her unoccupied hand and got a decent amount of their mixed cum, then she brought it to her mouth and licked it off "…much tastier." She stated as she swallowed.

"It also makes you look fucking hot." he said as he scooted closer to her and began to kiss her everywhere. Jessie rolled her eyes and laughed as she exhaled a nice smoke cloud from her mouth.

"As much as I love how you worship my body I need you to start getting ready, you're going to Sinnoh…I hear there's two or three legendary Pokémon there. So you know what you have to do." Jessie said.

"Yeah no problem baby, I'll get them for you." Ash replied while kissing her arm and shoulders.

"Good, now get going." She ordered.

"God I'm gunna miss you." he said sadly as he got off the bed and began putting his clothes back on.

Seeing him sad made Jessie want to motivate him "Well the faster you capture them the faster you can come back and…fuck Me." she told him seductively while biting her lip.

When he saw and heard her say that his dick twitched with arousal "Then can I use some of the Master balls that we stole?" he asked her, "Normally I wouldn't let you, but I'm gunna be horny the entire time you're away, so yes take some and hurry back." She answered while waving him off with her hand.

After hearing her say yes Ash was gone, he ran to the vault that contained all the legendary Pokémon he had caught for her, he dropped off the 3 new legendaries that he captured while he was there and went to the back where the master balls where at and got 3 of them. After that he went outside and unleashed Lugia once again, after hearing it roar he mounted it, and then ordered it to fly at top speed to Sinnoh.

As Jessie saw him fly away from her bedroom window she smiled happily, then she laid back, and once again got some of their mixed cum from her pussy on her hand and licked it clean.

"Hmmm… life is so wonderful... well my life certainly is." Jessie said to herself as she took another hit of her cigar before she exhaled it into the air above her and laughed in triumphed.

 **The End.**

* * *

 **Hope you guys enjoyed this little story. Now, because I wouldn't mind, I might do an Ash/Delia lemon/smut fic similar to this one. (Let me know if you guys would like to see one). It might take some time, mostly because I'm working on other stories, but I'll try to do another Pokémon fic. So yea… WolfDraco37 out.**


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